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A Protocol for Direct Stereospecific Amination of Primary, Secondary, and Tertiary Alkylboronic Esters

Emma K. Edelstein, Andrea C. Grote , Maximilian D. Palkowitz, James P. Morken*

*Department of Chemistry, Boston College, Chestnut Hill, MA 02467, USA, Email: morkenbc.edu

E. K. Edelstein, A. C. Grote, M. D. Palkowitz, J. P. Morken, Synlett, 2018, 29, 1749-1752.

DOI: 10.1055/s-0037-1610172 (free Supporting Information)


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Abstract

A direct, stereospecific amination of alkylboronic and borinic esters can be accomplished by treatment with methoxyamine and potassium tert-butoxide. In addition, this process also enables the direct amination of tertiary boronic esters in an efficient fashion.

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Direct Stereospecific Amination of Alkyl and Aryl Pinacol Boronates

S. N. Mlynarski, A. S. Karns, J. P. Morken, J. Am. Chem. Soc., 2012, 134, 16449-16451.


Key Words

organoboron, asymmetric synthesis, protected primary amines, amines, amination, chiral amines, stereochemistry


ID: J60-Y2018